If appreciation is not there, however, it seems like a potentially long waiting game to see if your $60k investment today returns anything meaningful in the long run. 

Meaningful home building hasn’t occurred in SoCal since the post war era.

However, from what I’ve observed, it’s still not enough to produce meaningful cash flow.

However if I do a BRRRR I can achieve infinite return by extracting all of my investment.

And Penny, the work you do as a social worker is so meaningful.

It’s awesome that you’re taking steps toward buying in an area you love and planning for the future—whether it’s as a second home or a long-term investment for your kids, this is a meaningful goal.

Just because you want to hit a specific number doesn't mean the market will meet you there.Great example of how Class C properties may appear like great cash flowing investments on paper - meaning fully rented, paying on time and normal levels of maintenance.

Welcome to the BP Community and most folks I know that are in your same situation with properties in 1 or more LLCs end up refinancing those properties into DSCR loans (instead of HELOCs) to extract the cash they need for their next acquisitions.

You cannot get any meaningful answers until you specify what is your "side gig", how much money it's going to bring and how much expenses it's going to incur, and what kind of expenses.And, as a rule of thumb, unless you clear $50k after all expenses, you probably will not benefit from any entities tax-wise. 

I don't know how the really big players stomach it.Something else I failed to mention was how the PM's are also tacking on fees on top of rent to extract even more money from our tenants.